Watersports & Boat Tours in Chicago

Chicago

Discover Chicago

Chicago offers a unique mix of urban excitement and waterfront relaxation. We recommend taking a boat tour along the Chicago River – the views of the skyline from the water are incredible. And if you have time, walking along the lakeshore or spending time in Millennium Park is always a great way to enjoy the city’s vibrant atmosphere.

Best things to do in Chicago

Typical things to do in Chicago are a visit to the Millennium Park to see “The Bean” and stroll along Navy Pier. The Art Institute of Chicago is a must-see, and shopping on Michigan Avenue is always fun. In the summer, you’ll find many festivals and live music to enjoy.

Getting around in Chicago

Chicago has an excellent public transportation system, including buses and trains. We’re also fans of renting bikes or walking to explore the downtown area.

The best Watersports & boat tours in Chicago

Take an architecture boat tour along the Chicago River for the best views of the skyline. Lake Michigan is great for sailing, paddleboarding, or renting kayaks for a day on the water.

AllSailing

Educational Sailing Tour in Chicago

Discover Chicago’s Skyline From a Sailboat

The best beaches in Chicago

When it’s time to hit the beach in Chicago, North Avenue Beach is where all the action happens. It’s bustling with families, volleyball players, and beachgoers, with plenty of space to soak in the sun. For a more central, city-meets-beach experience, Oak Street Beach offers amazing views of the Chicago skyline, right by the water. And if you’re in the mood for something quieter, Montrose Beach is a lovely option, especially for families. It’s got picnic areas and even a dog-friendly zone if you’re bringing a furry friend along.

Where and what to eat in Chicago

We recommend to try the typical deep-dish pizza at Lou Malnati’s or Giordano’s. For fine dining, Alinea offers a world-class culinary experience, and Chicago is famous for its hot dogs, which you can try at Portillo’s.

Amazing stories about Chicago

Where to stay in Chicago

The Windy City’s bustling energy is reflected in its variety of places to stay. In the heart of downtown, hotels around the Magnificent Mile and River North cater to those wanting easy access to shopping, dining, and cultural landmarks like Millennium Park. Looking for a more local experience? Head to neighborhoods like Wicker Park or Logan Square, where stylish boutique hotels and loft-style apartments offer a hip, artsy vibe. For lake views and a quieter atmosphere, the Gold Coast and Lakeshore Drive have great hotels with stunning views of Lake Michigan.

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